if he picks items whose provenance is tight, is of a player(s) who will likely remain a focus for collectors and he picks nice looking items that are pretty normal items to collect, he should be fine. Will he make a lot of money? There's no guarantees.
Autographs of guys like Ruth, Gehrig, Jackie Robinson, Roberto Clemente etc fit that. Signed baseballs are pretty standard items though a picture, book or other option may be cheaper.
Personally I prefer items that have a historical component to them as well (like items tied to jackie robinson and the integration or ties to WWII). I do think that besides for my personal interest, they have cross market appeal to non-sports collectors and should sustain value but of course if there is a premium there it may already be built into the price.
If I was spending 5k some items I'd consider:
- 1947 Dodgers team signed baseball
- nice Ruth or Gehrig autograph
If he wants to really speculate, find something of an early player who he thinks the Veterans committee may vote into the HOF.
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